TWI769856B - A liquid crystal composition comprising dibenzo derivatives and liquid crystal display device - Google Patents
A liquid crystal composition comprising dibenzo derivatives and liquid crystal display device Download PDFInfo
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- TWI769856B TWI769856B TW110121508A TW110121508A TWI769856B TW I769856 B TWI769856 B TW I769856B TW 110121508 A TW110121508 A TW 110121508A TW 110121508 A TW110121508 A TW 110121508A TW I769856 B TWI769856 B TW I769856B
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- liquid crystal
- crystal composition
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- carbon atoms
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 155
- 239000000203 mixture Substances 0.000 title claims abstract description 103
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000002834 transmittance Methods 0.000 abstract description 13
- 230000003287 optical effect Effects 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 abstract description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 125000003342 alkenyl group Chemical group 0.000 description 12
- -1 2-tetrahydrofuranyl Chemical group 0.000 description 10
- 238000012360 testing method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 4
- 230000001976 improved effect Effects 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 2
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- 125000005450 2,3-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C(F)=C(F)C([*:1])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/123—Ph-Ph-Ph
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-Cy
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- C09K19/00—Liquid crystal materials
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/301—Cy-Cy-Ph
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3016—Cy-Ph-Ph
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- C—CHEMISTRY; METALLURGY
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1343—Electrodes
- G02F1/134309—Electrodes characterised by their geometrical arrangement
- G02F1/134363—Electrodes characterised by their geometrical arrangement for applying an electric field parallel to the substrate, i.e. in-plane switching [IPS]
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13712—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering the liquid crystal having negative dielectric anisotropy
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- Optics & Photonics (AREA)
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- Liquid Crystal (AREA)
Abstract
本發明提供一種包含二苯並衍生物的液晶組合物及液晶顯示器件。所述液晶組合物包含至少一種通式I的化合物,以及至少一種通式II的化合物。與現有技術相比,本發明通過對通式I的化合物的結構優化,並與含有碳碳不飽和鍵的通式II的化合物協同作用,使所述液晶組合物在維持基本相當的清亮點、光學各向異性及介電各向異性的前提下,具有更高的垂直於分子軸的介電常數ε⊥ 、更高的垂直介電與介電絕對值的比值ε⊥ /|Δε|及更高的平均彈性常數Kave ,從而使包含該液晶組合物的液晶顯示器件具備更高的穿透率及更高的對比度,顯示效果更佳優異,在IPS模式、FFS模式及VA模式型液晶顯示器中具有較高的應用價值。The present invention provides a liquid crystal composition comprising a dibenzo derivative and a liquid crystal display device. The liquid crystal composition comprises at least one compound of general formula I, and at least one compound of general formula II. Compared with the prior art, the present invention optimizes the structure of the compound of the general formula I, and cooperates with the compound of the general formula II containing carbon-carbon unsaturated bonds, so that the liquid crystal composition maintains a substantially equivalent clearing point, Under the premise of optical anisotropy and dielectric anisotropy, it has a higher dielectric constant ε ⊥ perpendicular to the molecular axis, a higher ratio of the perpendicular dielectric to the absolute value of the dielectric ε ⊥ /|Δε| and more High average elastic constant K ave , so that the liquid crystal display device containing the liquid crystal composition has higher transmittance and higher contrast ratio, and the display effect is better and excellent. In IPS mode, FFS mode and VA mode liquid crystal display has high application value.
Description
本發明屬於液晶顯示材料技術領域,具體涉及一種包含二苯並衍生物的液晶組合物及液晶顯示器件。The invention belongs to the technical field of liquid crystal display materials, and particularly relates to a liquid crystal composition comprising dibenzo derivatives and a liquid crystal display device.
液晶顯示器(Liquid Crystal Display,LCD)因其體積小、重量輕、功耗低且顯示品質優異而獲得了飛速發展,特別是在可擕式電子資訊產品中獲得廣泛的應用。根據顯示模式的類型,可將液晶顯示器分為PC(phase change,相變)、TN(twist nematic,扭曲向列)、STN(super twisted nematic,超扭曲向列)、ECB(electrically controlled birefringence,電控雙折射)、OCB(optically compensated bend,光學補償彎曲)、IPS(in-plane switching,共面轉變)、FFS(fringe field switching,邊緣場切換)、VA(vertical alignment,垂直配向)及PSA(polymer stable alignment,聚合物穩定配向)等類型。Liquid Crystal Display (LCD) has developed rapidly because of its small size, light weight, low power consumption and excellent display quality, especially in portable electronic information products. According to the type of display mode, liquid crystal displays can be divided into PC (phase change, phase change), TN (twist nematic, twisted nematic), STN (super twisted nematic, super twisted nematic), ECB (electrically controlled birefringence, electrical controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching, coplanar transition), FFS (fringe field switching, fringe field switching), VA (vertical alignment, vertical alignment) and PSA ( polymer stable alignment, polymer stable alignment) and other types.
這些模式中,已知IPS模式、FFS模式及VA模式可改善TN模式、STN模式等動作模式視角窄的缺點。這些顯示模式的液晶顯示器主要使用具有負介電各向異性的液晶組合物。為進一步提高液晶顯示器的特性,所述組合物優選有下述(1)~(8)的物性: (1) 對熱、光等的高穩定性; (2) 高清亮點; (3) 液晶相的下限溫度低; (4) 低的黏度; (5) 適當的光學各向異性; (6) 負值大的介電各向異性; (7) 適當的彈性常數; (8) 液晶化合物的相容性良好。 液晶組合物的物性對液晶顯示器的顯示效果有重要影響。如,對熱、光等穩定性高的液晶組合物可增大液晶顯示器的電壓保持率,進而延長液晶顯示器的使用壽命;清亮點高、液晶相的下限溫度低的液晶組合物可擴大液晶顯示器的可使用的溫度範圍;黏度低的液晶組合物可縮短液晶顯示器的回應時間;具有適當的光學各向異性的液晶組合物可提高液晶顯示器的對比度,在液晶顯示器逐步向更薄的趨勢發展時,比較合適的是具有較大光學各向異性的液晶組合物;具有負值大的介電各向異性的液晶組合物可降低液晶顯示元件的閾值電壓,由此可降低電力消耗;彈性常數大的液晶組合物可縮短液晶顯示器的回應時間,彈性常數小的液晶組合物可降低液晶顯示器的閾值電壓;液晶化合物的相容性良好有利於將物性不同的液晶化合物混合來調節液晶組合物的物性。Among these modes, it is known that the IPS mode, the FFS mode and the VA mode can improve the shortcoming of the narrow viewing angle of the operation modes such as the TN mode and the STN mode. Liquid crystal displays of these display modes mainly use liquid crystal compositions having negative dielectric anisotropy. In order to further improve the characteristics of the liquid crystal display, the composition preferably has the following physical properties (1) to (8): (1) High stability to heat, light, etc.; (2) High-definition highlights; (3) The lower limit temperature of the liquid crystal phase is low; (4) Low viscosity; (5) Appropriate optical anisotropy; (6) Dielectric anisotropy with a large negative value; (7) Appropriate elastic constant; (8) The compatibility of the liquid crystal compound is good. The physical properties of the liquid crystal composition have an important influence on the display effect of the liquid crystal display. For example, liquid crystal compositions with high stability to heat and light can increase the voltage holding ratio of liquid crystal displays, thereby prolonging the service life of liquid crystal displays; liquid crystal compositions with high clearing point and low lower limit temperature of liquid crystal phase can expand liquid crystal displays. The usable temperature range of the liquid crystal display; the liquid crystal composition with low viscosity can shorten the response time of the liquid crystal display; the liquid crystal composition with appropriate optical anisotropy can improve the contrast ratio of the liquid crystal display, when the liquid crystal display is gradually developing towards a thinner trend , the liquid crystal composition with large optical anisotropy is more suitable; the liquid crystal composition with large negative dielectric anisotropy can reduce the threshold voltage of the liquid crystal display element, thereby reducing power consumption; large elastic constant The liquid crystal composition can shorten the response time of the liquid crystal display, and the liquid crystal composition with small elastic constant can reduce the threshold voltage of the liquid crystal display; the good compatibility of the liquid crystal compound is conducive to the mixing of liquid crystal compounds with different physical properties to adjust the physical properties of the liquid crystal composition .
另外,提升液晶顯示器的對比度也是業內不斷研究的目標之一。研究表明,影響液晶顯示元件的對比度的最主要因素為液晶材料的漏光,而影響漏光的主要因素是液晶材料的光散射(LC Scattering),而LC Scattering與平均彈性常數Kave 的關係式如下: LC Scattering ∝, 其中,d表示液晶盒的間距,ne 表示非尋常光折射率,no 表示尋常光折射率。由該關係式可知,LC Scattering與Kave 成反比例,在提高Kave 的情況下,可以降低液晶材料的漏光。 此外,對比度(CR)與亮度(L)的關係式如下: CR=L255 /L0 ×100%, 其中,L255 為開態亮度,L0 為關態亮度。可以看出,顯著影響CR的應該是L0 的變化。關態下,L0 與液晶分子的介電無關,與液晶材料本身的LC Scattering相關,LC Scattering愈小,L0 也愈小,CR從而也就會顯著提高。In addition, improving the contrast ratio of liquid crystal displays is also one of the goals of continuous research in the industry. Studies have shown that the most important factor affecting the contrast of liquid crystal display elements is the light leakage of the liquid crystal material, and the main factor affecting the light leakage is the light scattering (LC Scattering) of the liquid crystal material, and the relationship between LC Scattering and the average elastic constant Kave is as follows: LC Scattering ∝ , where d represents the spacing of the liquid crystal cells, ne represents the refractive index of extraordinary light, and no represents the refractive index of ordinary light. It can be seen from this relational expression that LC Scattering is inversely proportional to Kave , and when the Kave is increased, the light leakage of the liquid crystal material can be reduced. In addition, the relationship between the contrast ratio (CR) and the brightness (L) is as follows: CR=L 255 /L 0 ×100%, where L 255 is the on-state brightness, and L 0 is the off-state brightness. It can be seen that it should be the change in L 0 that significantly affects CR. In the off state, L 0 has nothing to do with the dielectric of the liquid crystal molecules, but is related to the LC Scattering of the liquid crystal material itself.
另外,目前的液晶顯示器件還存在功耗高的問題,這是因為只有大約5%左右的背光能夠穿透顯示器件而被人眼捕獲,絕大部分光是被“浪費”了的。如果能夠開發出光穿透率高的液晶,即能夠降低背光強度,從而實現節省能耗的目的,延長設備的使用時間。In addition, the current liquid crystal display device still has the problem of high power consumption, because only about 5% of the backlight can penetrate the display device and be captured by the human eye, and most of the light is "wasted". If a liquid crystal with high light transmittance can be developed, the intensity of the backlight can be reduced, so as to achieve the purpose of saving energy consumption and prolong the use time of the device.
中國公開專利CN107973766A公開了一種含有環烷基的氧芴衍生物的液晶化合物,結構如下式A所示:A, 其中,H表示環丙基、環丁基、環戊基或2-四氫呋喃基中的一種;Z表示單鍵、-CH2 -、-O-、-CH2 CH2 -或-CH2 O-中的一種;X表示氫原子、氟原子、碳原子數為1-7的烷基或碳原子數為1-7的烷氧基的一種。Chinese published patent CN107973766A discloses a liquid crystal compound containing a cycloalkyl oxofluorene derivative, the structure of which is shown in the following formula A: A, wherein, H represents one of cyclopropyl, cyclobutyl, cyclopentyl or 2-tetrahydrofuranyl; Z represents a single bond, -CH 2 -, -O-, -CH 2 CH 2 - or -CH 2 One of O-; X represents one of hydrogen atom, fluorine atom, alkyl group with 1-7 carbon atoms or alkoxy group with 1-7 carbon atoms.
上述具有環烷基的氧芴衍生物的液晶化合物與其他液晶化合物互溶性好,低溫穩定性也相應提高。然而包含該類化合物的液晶組合物的穿透率卻有待進一步提高。The above-mentioned liquid crystal compound of the oxofluorene derivative having a cycloalkyl group has good compatibility with other liquid crystal compounds, and the low temperature stability is also improved accordingly. However, the transmittance of liquid crystal compositions containing such compounds needs to be further improved.
因此,在現有技術的基礎上,期待開發一種具有更高穿透率、更高對比的液晶組合物,從而能夠滿足液晶顯示器越來越高的視覺效果及低功耗的需求。Therefore, on the basis of the prior art, it is expected to develop a liquid crystal composition with higher transmittance and higher contrast, so as to be able to meet the increasingly high visual effect and low power consumption requirements of liquid crystal displays.
針對現有技術中存在的缺陷,本發明的目的在於提供一種包含二苯並衍生物的液晶組合物及液晶顯示器件,所述液晶組合物具有高的清亮點、大的光學各向異性、大的介電各向異性、較高的垂直於分子軸的介電常數ε⊥ 、較高的垂直介電與介電絕對值的比值ε⊥ /|Δε|及較高的平均彈性常數Kave 。In view of the defects existing in the prior art, the purpose of the present invention is to provide a liquid crystal composition comprising a dibenzo derivative and a liquid crystal display device, the liquid crystal composition has a high clearing point, a large optical anisotropy, a large Dielectric anisotropy, higher dielectric constant ε ⊥ perpendicular to the molecular axis, higher ratio of perpendicular dielectric to absolute value of dielectric ε ⊥ /|Δε| and higher average elastic constant Kave .
為了實現上述發明目的,本發明採用以下技術方案:In order to realize the above-mentioned purpose of the invention, the present invention adopts the following technical solutions:
第一方面,本發明提供一種包含二苯並衍生物的液晶組合物,所述液晶組合物包含至少一種通式I的化合物,以及至少一種通式II的化合物:
本發明中,所述1-12個碳原子可以為1、2、3、4、5、6、7、8、9、10、11或12個碳原子。In the present invention, the 1-12 carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms.
本發明的碳碳不飽和鍵為-CH=CH-或-C≡C-,例如,R1 表示CH2 =CH-,或者環表示,或者Z3 表示-CH=CH-,等等。The carbon-carbon unsaturated bond of the present invention is -CH=CH- or -C≡C-, for example, R 1 represents CH 2 =CH-, or a ring express , or Z 3 for -CH=CH-, etc.
當n=2時,化合物中存在兩個,這兩個可以具有相同的結構也可以具有不同的結構,示例性地,可以一個為,另一個為;本發明涉及到“相同或不同”的表述時,均具有同樣的意義。When n=2, there are two , the two can have the same structure or different structures, for example, one can be , the other is ; When the present invention relates to the expression "same or different", all have the same meaning.
本發明中,“可分別獨立地被……替代”指的是可以被替代,也可以不被替代,即,替代或不被替代,均屬於本發明的保護範圍之內,“可分別獨立地被……取代”同理,且“替代”和“取代”的位置可以是任意的。In the present invention, "can be replaced independently by ..." means that it can be replaced or not replaced, that is, replacement or non-replacement belongs to the protection scope of the present invention. The same is true for "replaced by", and the positions of "replacement" and "replacement" can be arbitrary.
本發明中,基團結構一側或兩側的短直線代表接入鍵,不代表甲基,例如右側的短直線、兩側的短直線。In the present invention, the short straight lines on one side or both sides of the group structure represent access bonds, not methyl groups, for example The short straight line on the right, Short straight lines on both sides.
本發明中,所述鹵素包括氟、氯、溴或碘等。In the present invention, the halogen includes fluorine, chlorine, bromine or iodine and the like.
本發明的通式I的化合物中,環為氧雜五元環或硫雜五元環的結構,相對環為五元碳環的現有技術來說,本發明的通式I的化合物具有較大的垂直於分子軸的介電常數ε⊥ ,更有利於在維持介電各向異性不變的前提下,提升液晶組合物的垂直介電與介電絕對值的比值ε⊥ /|Δε|,從而實現提升液晶組合物穿透率的效果;另外,本發明的通式I的化合物還具有較大的平均彈性常數Kave ,使得包含本發明液晶組合物的液晶顯示器件在暗態時的漏光更小,對比度更高。In the compound of the general formula I of the present invention, the ring It is the structure of oxa five-membered ring or thia five-membered ring, the opposite ring For the prior art of the five-membered carbocyclic ring, the compound of the general formula I of the present invention has a larger dielectric constant ε ⊥ perpendicular to the molecular axis, which is more conducive to maintaining the dielectric anisotropy unchanged. The ratio ε ⊥ /|Δε| of the vertical dielectric to the absolute value of the dielectric of the liquid crystal composition is improved, so as to achieve the effect of improving the transmittance of the liquid crystal composition; in addition, the compound of the general formula I of the present invention also has a larger average The elastic constant Kave enables the liquid crystal display device comprising the liquid crystal composition of the present invention to have smaller light leakage and higher contrast in the dark state.
本發明還驚喜地發現,通式I的化合物中,Z1 為亞烷氧基或亞烷硫基的結構,相對Z1 表示直鏈亞烷基的技術方案來說,通式I的化合物體現出來的整體共軛作用更強,分子內部基團協同作用後,垂直介電與介電絕對值的比值ε⊥ /|Δε|及平均彈性常數Kave 均有較明顯的提升作用,更有利於實現本發明穿透率高、對比度高的效果。The present invention also surprisingly finds that, in the compound of the general formula I, Z 1 is the structure of an alkyleneoxy group or an alkylenethio group. Compared with the technical solution in which Z 1 represents a straight-chain alkylene group, the compound of the general formula I embodies The resulting overall conjugation is stronger. After the synergistic effect of the intramolecular groups, the ratio of the vertical dielectric to the absolute value of the dielectric ε ⊥ /|Δε| and the average elastic constant Kave have a significantly improved effect, which is more conducive to The effects of high transmittance and high contrast of the present invention are achieved.
在本發明的優選實施方案中,所述n表示0。In a preferred embodiment of the present invention, the n represents 0.
在本發明的優選實施方案中,所述L1 和L2 均表示-F。In a preferred embodiment of the present invention, both L 1 and L 2 represent -F.
在本發明的優選實施方案中,所述X表示-O-或-S-。In a preferred embodiment of the present invention, the X represents -O- or -S-.
在本發明的優選實施方案中,所述液晶組合物中含有至少一種X表示-O-的通式I的化合物;進一步優選地,所述液晶組合物中含有至少一種X表示-O-的通式I的化合物,以及至少一種X表示-S-的通式I的化合物。In a preferred embodiment of the present invention, the liquid crystal composition contains at least one compound of formula I whose X represents -O-; further preferably, the liquid crystal composition contains at least one compound whose X represents -O- Compounds of formula I, and at least one compound of general formula I wherein X represents -S-.
在本發明的優選實施方案中,所述a表示0至3的整數,例如0、1、2或3;進一步優選地,a表示1至3的整數,再進一步優選地,a表示1。In a preferred embodiment of the present invention, the a represents an integer from 0 to 3, such as 0, 1, 2 or 3; further preferably, a represents an integer from 1 to 3, and still further preferably, a represents 1.
在本發明的優選實施方案中,所述R表示含有1-12(例如1、2、3、4、5、6、8、10或11等)個碳原子的直鏈或支鏈烷基,或所述含有1-12(例如1、2、3、4、5、6、8、10或11等)個碳原子的直鏈或支鏈烷基中的一個或不相鄰的至少兩個-CH2 -可分別獨立地被-O-或-S-替代。In a preferred embodiment of the present invention, said R represents a straight or branched chain alkyl group containing 1-12 (eg 1, 2, 3, 4, 5, 6, 8, 10 or 11 etc.) carbon atoms, Or one or at least two non-adjacent straight or branched chain alkyl groups containing 1-12 (eg 1, 2, 3, 4, 5, 6, 8, 10 or 11, etc.) carbon atoms -CH 2 - can be independently replaced by -O- or -S-, respectively.
在本發明的優選實施方案中,所述R表示含有1-12(例如1、2、3、4、5、6、8、10或11等)個碳原子的直鏈烷基或烷氧基。In a preferred embodiment of the present invention, said R represents a straight chain alkyl or alkoxy group containing 1-12 (eg 1, 2, 3, 4, 5, 6, 8, 10 or 11 etc.) carbon atoms .
在本發明的優選實施方案中,所述Rx 表示-H、含有1-12(例如1、2、3、4、5、6、8、10或11等)個碳原子的直鏈或支鏈的烷基。In a preferred embodiment of the present invention, said R x represents -H, a linear or branched chain containing 1-12 (eg 1, 2, 3, 4, 5, 6, 8, 10 or 11 etc.) carbon atoms chain alkyl.
在本發明的優選實施方案中,所述Rx 表示-H或含有1-6個碳原子的直鏈烷基。In a preferred embodiment of the present invention, said R x represents -H or a straight chain alkyl group containing 1-6 carbon atoms.
在本發明的優選實施方案中,所述通式I的化合物占液晶組合物總重量的0.1-40%,例如0.2%、0.5%、0.8%、1%、3%、5%、8%、10%、12%、15%、18%、20%、22%、25%、28%、30%、32%、35%、37%或39%等;進一步優選地,所述通式I的化合物占液晶組合物總重量的1-30%。In a preferred embodiment of the present invention, the compound of general formula I accounts for 0.1-40% of the total weight of the liquid crystal composition, such as 0.2%, 0.5%, 0.8%, 1%, 3%, 5%, 8%, 10%, 12%, 15%, 18%, 20%, 22%, 25%, 28%, 30%, 32%, 35%, 37% or 39%, etc.; further preferably, the general formula I The compound accounts for 1-30% of the total weight of the liquid crystal composition.
在本發明的優選實施方案中,所述通式II的化合物滿足如下條件a)~c)中的至少其一: a)R1 表示含有2-10(例如2、3、4、5、6、8、9或10)個碳原子的烯基或烯氧基; b)當m表示1或2時,至少一個環表示、或; c)當m表示1或2時,至少一個Z3 表示-CH=CH-或-C≡C-。In a preferred embodiment of the present invention, the compound of the general formula II satisfies at least one of the following conditions a) to c): a) R 1 represents a compound containing 2-10 (eg 2, 3, 4, 5, 6 , 8, 9 or 10) an alkenyl or alkenyloxy group of carbon atoms; b) when m represents 1 or 2, at least one ring express , or ; c) When m represents 1 or 2, at least one Z 3 represents -CH=CH- or -C≡C-.
本發明中的烯基優選為式(V1)至式(V9)中的任意一者所表示的基團,特別優選為式(V1)、式(V2)、式(V8)或(V9)。式(V1)至式(V9)所表示的基團如下所示: , 其中,*表示上述基團與化合物的連接位點。The alkenyl group in the present invention is preferably a group represented by any one of formulae (V1) to (V9), and particularly preferably formula (V1), formula (V2), formula (V8) or (V9). The groups represented by formula (V1) to formula (V9) are as follows: , wherein, * represents the linking site of the above-mentioned group and the compound.
本發明中的烯氧基優選為式(OV1)至式(OV9)中的任意一者所表示的基團,特別優選為式(OV1)、式(OV2)、式(OV8)或(OV9)。式(OV1)至式(OV9)所表示的基團如下所示: , 其中,*表示上述基團與化合物的連接位點。The alkenyloxy group in the present invention is preferably a group represented by any one of formula (OV1) to formula (OV9), particularly preferably formula (OV1), formula (OV2), formula (OV8) or (OV9) . The groups represented by formula (OV1) to formula (OV9) are as follows: , wherein, * represents the linking site of the above-mentioned group and the compound.
在本發明的優選實施方案中,所述通式II的化合物選自由如下化合物組成的組:II-1;II-2;II-3;II-4;II-5;II-6;II-7;II-8;II-9;II-10;以及II-11, 其中, Ralkenyl 表示含有2-7(例如2、3、4、5、6或7)個碳原子的烯基; R1 和R2 各自獨立地表示含有1-10(例如1、2、3、4、5、6、7、8、9或10)個碳原子的直鏈的烷基或烷氧基,或者含有2-10(例如2、3、4、5、6、7、8、9或10)個碳原子的直鏈的烯基或烯氧基。In a preferred embodiment of the present invention, the compound of general formula II is selected from the group consisting of: II-1; II-2; II-3; II-4; II-5; II-6; II-7; II-8; II-9; II-10; and II-11, wherein, R alkenyl represents an alkenyl group containing 2-7 (eg 2, 3, 4, 5, 6 or 7) carbon atoms; R 1 and R 2 each independently represent a group containing 1-10 (eg 1 , 2, 3, 4, 5, 6, 7, 8, 9 or 10) carbon atoms straight-chain alkyl or alkoxy group, or containing 2-10 (such as 2, 3, 4, 5, 6, 7, 8, 9 or 10) straight-chain alkenyl or alkenyloxy groups.
在本發明的優選實施方案中,所述通式II的化合物占液晶組合物總重量的0.1-50%,例如0.2%、0.5%、0.8%、1%、3%、5%、8%、10%、12%、15%、18%、20%、22%、25%、28%、30%、32%、35%、37%、39%、40%、42%、45%、47%或49%等;進一步優選地,所述通式II的化合物占液晶組合物總重量的1-45%,再進一步優選地,所述通式II的化合物占液晶組合物總重量的5-43%。In a preferred embodiment of the present invention, the compound of general formula II accounts for 0.1-50% of the total weight of the liquid crystal composition, such as 0.2%, 0.5%, 0.8%, 1%, 3%, 5%, 8%, 10%, 12%, 15%, 18%, 20%, 22%, 25%, 28%, 30%, 32%, 35%, 37%, 39%, 40%, 42%, 45%, 47% or 49%, etc.; further preferably, the compound of the general formula II accounts for 1-45% of the total weight of the liquid crystal composition, and further preferably, the compound of the general formula II accounts for 5-43% of the total weight of the liquid crystal composition %.
在本發明的優選實施方案中,所述液晶組合物中還包含一種或至少兩種通式M的化合物M, 其中, RM1 和RM2 各自獨立地表示含有1-12(例如1、2、3、4、5、6、8、10或11等)個碳原子的直鏈或支鏈的烷基、、或,所述含有1-12個碳原子的直鏈或支鏈的烷基中的一個或不相鄰的至少兩個-CH2 -可分別獨立地被-CH=CH-、-C≡C-、-O-、-CO-、-CO-O-或-O-CO-替代; 環、環和環各自獨立地表示或,所述中的一個或至少兩個-CH2 -可被-O-替代,所述中的至多一個-H可被鹵素取代; ZM1 和ZM2 各自獨立地表示單鍵、-CO-O-、-O-CO-、-CH2 O-、-OCH2 -、-CH=CH-、-C≡C-、-CH2 CH2 -、-(CH2 )4 -、-CF2 O-、-OCF2 -或-CF2 CF2 -; nM1 表示0、1、2或3,其中當nM1 =2或3時,環相同或不同,ZM2 相同或不同。In a preferred embodiment of the present invention, the liquid crystal composition further comprises one or at least two compounds of the general formula M M, wherein R M1 and R M2 each independently represent a linear or branched alkyl group containing 1-12 (eg, 1, 2, 3, 4, 5, 6, 8, 10, or 11, etc.) carbon atoms , , or , one or non-adjacent at least two -CH 2 - in the linear or branched alkyl group containing 1-12 carbon atoms can be independently replaced by -CH=CH-, -C≡C- , -O-, -CO-, -CO-O- or -O-CO- substitution; ring ,ring and ring represent independently or , the One or at least two of -CH 2 - can be replaced by -O-, the At most one -H in the can be substituted by halogen; Z M1 and Z M2 each independently represent a single bond, -CO-O-, -O-CO-, -CH 2 O-, -OCH 2 -, -CH=CH -, -C≡C-, -CH 2 CH 2 -, -(CH 2 ) 4 -, -CF 2 O-, -OCF 2 - or -CF 2 CF 2 -; n M1 represents 0, 1, 2 or 3, where when n M1 = 2 or 3, the ring Same or different, same or different Z M2 .
在本發明的優選實施方案中,所述RM1 和RM2 各自獨立地表示含有1-10(例如1、2、3、4、5、6、8、9或10)個碳原子的直鏈的烷基、含有1-9(例如1、2、3、4、5、6、8或9)個碳原子的直鏈的烷氧基、或含有2-10(例如2、3、4、5、6、8、9或10)個碳原子的直鏈的烯基。In a preferred embodiment of the present invention, said R M1 and R M2 each independently represent a straight chain containing 1-10 (eg 1, 2, 3, 4, 5, 6, 8, 9 or 10) carbon atoms alkyl, straight-chain alkoxy containing 1-9 (such as 1, 2, 3, 4, 5, 6, 8 or 9) carbon atoms, or containing 2-10 (such as 2, 3, 4, 5, 6, 8, 9 or 10) straight chain alkenyl.
進一步優選地,所述RM1 和RM2 各自獨立地表示含有1-8個碳原子的直鏈的烷基、含有1-7個碳原子的直鏈的烷氧基或含有2-8個碳原子的直鏈的烯基。Further preferably, said R M1 and R M2 each independently represent a straight-chain alkyl group containing 1-8 carbon atoms, a straight-chain alkoxy group containing 1-7 carbon atoms or a straight-chain alkoxy group containing 2-8 carbon atoms. Atomic straight-chain alkenyl.
再進一步優選地,RM1 和RM2 各自獨立地表示含有1-5個碳原子的直鏈的烷基、含有1-4個碳原子的直鏈的烷氧基或含有2-5個碳原子的直鏈的烯基。Still further preferably, R M1 and R M2 each independently represent a straight-chain alkyl group containing 1-5 carbon atoms, a straight-chain alkoxy group containing 1-4 carbon atoms or a straight-chain alkoxy group containing 2-5 carbon atoms. straight-chain alkenyl.
在本發明的優選實施方案中,所述RM1 和RM2 中的任意一者為含有2-5個碳原子的直鏈的烯基,而另一者為含有1-5個碳原子的直鏈的烷基。In a preferred embodiment of the present invention, any one of the R M1 and R M2 is a straight-chain alkenyl group containing 2-5 carbon atoms, and the other is a straight-chain alkenyl group containing 1-5 carbon atoms chain alkyl.
在本發明的優選實施方案中,所述RM1 和RM2 中的任意一者為含有1-5個碳原子的直鏈的烷基,而另一者為含有1-5個碳原子的直鏈的烷基或含有1-4個碳原子的直鏈的烷氧基;進一步優選地,RM1 和RM2 兩者均各自獨立地為含有1-5個碳原子的直鏈的烷基。In a preferred embodiment of the present invention, either one of said R M1 and R M2 is a straight-chain alkyl group containing 1-5 carbon atoms, and the other is a straight-chain alkyl group containing 1-5 carbon atoms A chain alkyl group or a straight-chain alkoxy group containing 1-4 carbon atoms; further preferably, both R M1 and R M2 are each independently a straight-chain alkyl group containing 1-5 carbon atoms.
在本發明的優選實施方案中,所述通式M的化合物選自由如下化合物組成的組:
優選地,所述RM1 和RM2 各自獨立地表示含有1-10(例如1、2、3、4、5、6、8、9或10)個碳原子的直鏈烷基、含有2-10(例如2、3、4、5、6、8、9或10)個碳原子的直鏈烯基或含有1-9(例如1、2、3、4、5、6、8或9)個碳原子的直鏈烷氧基。Preferably, said R M1 and R M2 each independently represent a straight-chain alkyl group containing 1-10 (eg 1, 2, 3, 4, 5, 6, 8, 9 or 10) carbon atoms, a 2- 10 (e.g. 2, 3, 4, 5, 6, 8, 9 or 10) carbon atoms straight chain alkenyl or containing 1-9 (e.g. 1, 2, 3, 4, 5, 6, 8 or 9) A straight-chain alkoxy group of carbon atoms.
優選地,所述通式M的化合物占液晶組合物總重量的1-70%,例如2%、4%、6%、8%、10%、13%、15%、18%、20%、22%、25%、28%、30%、33%、35%、38%、40%、43%、45%、48%、50%、52%、55%、58%、60%、62%、65%、67%或69%等。Preferably, the compound of general formula M accounts for 1-70% of the total weight of the liquid crystal composition, such as 2%, 4%, 6%, 8%, 10%, 13%, 15%, 18%, 20%, 22%, 25%, 28%, 30%, 33%, 35%, 38%, 40%, 43%, 45%, 48%, 50%, 52%, 55%, 58%, 60%, 62% , 65%, 67% or 69%, etc.
為了調節液晶組合物的清亮點、粘度及低溫存儲穩定性等方面的性能,以使獲得的液晶顯示器件除了在透過率和色彩表現方面表現優異外,還具有更好的應用價值,需要調節液晶組合物的組分構成;具體地,相對於本發明的液晶組合物的總重量,其中環表示的通式M的化合物的含量為10-50%;優選地,其中環表示的通式M的化合物的含量為20-45%。In order to adjust the properties of the liquid crystal composition in terms of clearing point, viscosity and low temperature storage stability, so that the obtained liquid crystal display device not only has excellent transmittance and color performance, but also has better application value, it is necessary to adjust the liquid crystal The composition of the composition; specifically, with respect to the total weight of the liquid crystal composition of the present invention, wherein the ring express The content of the compound of general formula M is 10-50%; preferably, wherein the ring express The content of the compound of general formula M is 20-45%.
關於通式M的化合物的含量,在需要保持本發明的液晶組合物粘度較低且回應時間較短時,優選其下限值較高且上限值較高;進一步地,在需要保持本發明的液晶組合物的清亮點較高且溫度穩定性良好時,優選其下限值較高且上限值較高;在為了將驅動電壓保持為較低且介電各向異性的絕對值變大時,優選使其下限值變低且上限值變低。Regarding the content of the compound of the general formula M, when the viscosity of the liquid crystal composition of the present invention needs to be kept low and the response time is short, preferably the lower limit value is higher and the upper limit value is higher; further, when it is necessary to keep the present invention When the clearing point of the liquid crystal composition is high and the temperature stability is good, the lower limit value is preferably high and the upper limit value is high; in order to keep the driving voltage low and the absolute value of the dielectric anisotropy becomes large , it is preferable to make the lower limit value lower and the upper limit value lower.
在重視可靠性的情形時,優選RM1 和RM2 均各自獨立地為烷基;在重視降低化合物的揮發性的情形時,優選RM1 和RM2 均各自獨立地為烷氧基;在重視粘度降低的情形時,優選RM1 和RM2 中至少一者為烯基。In the case of attaching importance to reliability, it is preferable that both R M1 and R M2 are independently an alkyl group; in the case of attaching importance to reducing the volatility of the compound, it is preferable that both R M1 and R M2 are each independently an alkoxy group; When the viscosity is lowered, at least one of R M1 and R M2 is preferably an alkenyl group.
在本發明的優選實施方案中,為了進一步降低液晶組合物的黏度,液晶組合物優選包含一種或更多種其中RM1
和/或RM2
為正丙基的通式M1的化合物
在本發明的優選實施方案中,所述RN1 和RN2 各自獨立地表示含有1-8(例如1、2、3、4、5、6、7或8)個碳原子的直鏈或支鏈的烷基或烷氧基,進一步優選地,所述RN1 和RN2 各自獨立地為含有1-5個碳原子的直鏈或支鏈的烷基或烷氧基。In a preferred embodiment of the present invention, said R N1 and R N2 each independently represent a straight or branched chain containing 1-8 (eg 1, 2, 3, 4, 5, 6, 7 or 8) carbon atoms chain alkyl or alkoxy, further preferably, the R N1 and R N2 are each independently a linear or branched alkyl or alkoxy containing 1-5 carbon atoms.
在本發明的優選實施方案中,所述環和環各自獨立地表示、、、、、、、或。In a preferred embodiment of the present invention, the ring and ring represent independently , , , , , , , or .
在本發明的優選實施方案中,所述通式N的化合物選自由如下化合物組成的組:
在本發明的優選實施方案中,通式N的化合物優選自由通式N2、通式N5、通式N13的化合物組成的組。In a preferred embodiment of the present invention, the compound of general formula N is preferably selected from the group consisting of compounds of general formula N2, general formula N5, general formula N13.
優選地,所述通式N的化合物占液晶組合物總重量的1-75%,例如2%、4%、6%、8%、10%、13%、15%、18%、20%、22%、25%、28%、30%、33%、35%、38%、40%、43%、45%、48%、50%、52%、55%、58%、60%、62%、65%、67%、70%、72%或74%等。Preferably, the compound of general formula N accounts for 1-75% of the total weight of the liquid crystal composition, such as 2%, 4%, 6%, 8%, 10%, 13%, 15%, 18%, 20%, 22%, 25%, 28%, 30%, 33%, 35%, 38%, 40%, 43%, 45%, 48%, 50%, 52%, 55%, 58%, 60%, 62% , 65%, 67%, 70%, 72% or 74%, etc.
關於通式N的化合物含量,在需要保持本發明的液晶顯示器件回應時間較短時,優選其下限值較低且上限值較低;進一步地,在需要保持本發明的液晶顯示器件工作溫度範圍更寬時,優選其下限值較低且上限值較低;另外,在為了將液晶組合物的驅動電壓保持為較低而使介電各向異性的絕對值變大時,優選使其下限值變高且上限值較高。Regarding the content of the compound of the general formula N, when the response time of the liquid crystal display device of the present invention needs to be kept short, the lower limit value and the upper limit value are preferably lower; further, when it is necessary to keep the liquid crystal display device of the present invention working When the temperature range is wider, the lower limit value is preferably lower and the upper limit value is lower; in addition, when the absolute value of the dielectric anisotropy is increased in order to keep the driving voltage of the liquid crystal composition low, it is preferably Make its lower limit value higher and its upper limit value higher.
在本發明的優選實施方案中,可以向液晶組合物中添加本領域技術人員已知和文獻中描述的一種或更多種其他添加劑。In a preferred embodiment of the present invention, one or more other additives known to those skilled in the art and described in the literature may be added to the liquid crystal composition.
另外,本發明的液晶組合物中所使用的抗氧化劑、光穩定劑等添加劑優選以下物質:
優選地,穩定劑選自如下所示的穩定劑。
在本發明的優選實施方案中,穩定劑占液晶組合物總重量的0-5%;優選地,穩定劑占液晶組合物總重量的0-1%;更優選地,穩定劑占液晶組合物總重量的0.01-0.1%。In a preferred embodiment of the present invention, the stabilizer accounts for 0-5% of the total weight of the liquid crystal composition; preferably, the stabilizer accounts for 0-1% of the total weight of the liquid crystal composition; more preferably, the stabilizer accounts for the liquid crystal composition 0.01-0.1% of the total weight.
另一方面,本發明提供一種包含如上所述的液晶組合物的液晶顯示器件。In another aspect, the present invention provides a liquid crystal display device comprising the liquid crystal composition as described above.
優選地,所述液晶顯示器件為IPS模式型液晶顯示器件、FFS模式型液晶顯示器件或VA模式型液晶顯示器件。Preferably, the liquid crystal display device is an IPS mode liquid crystal display device, an FFS mode liquid crystal display device or a VA mode liquid crystal display device.
相對於現有技術,本發明具有以下有益效果: 與現有技術相比,本發明提供的液晶組合物中,通過對通式I的化合物的結構優化,並與含有碳碳不飽和鍵的通式II的化合物協同作用,使本發明所述液晶組合物在維持基本相當的清亮點、光學各向異性及介電各向異性的前提下,具有更高的垂直於分子軸的介電常數ε⊥ 、更高的垂直介電與介電絕對值的比值ε⊥ /|Δε|及更高的平均彈性常數Kave ,從而使包含該液晶組合物的液晶顯示器件具備更高的穿透率及更高的對比度,顯示效果更佳優異,在IPS模式、FFS模式及VA模式型液晶顯示器中具有較高的應用價值。Compared with the prior art, the present invention has the following beneficial effects: Compared with the prior art, in the liquid crystal composition provided by the present invention, by optimizing the structure of the compound of the general formula I, and with the general formula II containing carbon-carbon unsaturated bonds The synergistic effect of the compounds enables the liquid crystal composition of the present invention to have a higher dielectric constant ε ⊥ perpendicular to the molecular axis on the premise of maintaining substantially equivalent clearing point, optical anisotropy and dielectric anisotropy. Higher ratio of vertical dielectric to absolute value of dielectric ε ⊥ /|Δε| and higher average elastic constant Kave , so that the liquid crystal display device comprising the liquid crystal composition has higher transmittance and higher The contrast ratio is better and the display effect is better and excellent, and it has high application value in IPS mode, FFS mode and VA mode liquid crystal display.
以下將結合具體實施方式來進一步說明本發明的技術方案。本領域技術人員應該明瞭,以下實施例為本發明的示例,僅用來說明和幫助理解本發明,不應視為對本發明的限制。在不偏離本發明主旨或範圍的情況下,可進行本發明構思內的其他組合和各種改良。The technical solutions of the present invention will be further described below in conjunction with specific embodiments. It should be understood by those skilled in the art that the following embodiments are examples of the present invention, are only used to illustrate and help the understanding of the present invention, and should not be regarded as a limitation of the present invention. Other combinations and various modifications within the inventive concept can be made without departing from the spirit or scope of the inventions.
在本發明中如無特殊說明,本發明中提及的比例均為重量比,所有溫度均為攝氏溫度。Unless otherwise specified in the present invention, the ratios mentioned in the present invention are all weight ratios, and all temperatures are degrees Celsius.
為便於表達,以下各實施例中,液晶化合物的基團結構用表1所列的代碼表示:
表1 液晶化合物的基團結構代碼
以如下結構式的化合物為例: 該結構式如用表1所列代碼表示,則可表達為:nCCGF,代碼中的n表示左端烷基的C原子數,例如n為“3”,即表示該烷基為-C3 H7 ;代碼中的C代表1,4-亞環己基,G代表2-氟-1,4-亞苯基,F代表氟取代基。Take the compound of the following structural formula as an example: If the structural formula is represented by the codes listed in Table 1, it can be expressed as: nCCGF, where n in the code represents the number of C atoms of the left-terminal alkyl group, for example, n is "3", which means that the alkyl group is -C 3 H 7 ; C in the code represents 1,4-cyclohexylene, G represents 2-fluoro-1,4-phenylene, and F represents fluorine substituent.
以下實施例中測試專案的簡寫代號如下:
在以下的實施例中所採用的各成分,均可以通過公知的方法進行合成,或者通過商業途徑獲得。這些合成技術是常規的,所得到各液晶組合物經測試符合電子類化合物標準。The components used in the following examples can be synthesized by known methods or obtained through commercial channels. These synthesis techniques are conventional, and each of the resulting liquid crystal compositions has been tested to meet electronic compound standards.
按照以下實施例規定的各液晶組合物的配比製備液晶組合物。液晶組合物的製備是按照本領域的常規方法進行的,如採取加熱、超聲波、懸浮等方式按照規定比例混合制得。The liquid crystal compositions were prepared according to the proportions of the liquid crystal compositions specified in the following examples. The preparation of the liquid crystal composition is carried out according to the conventional methods in the art, such as heating, ultrasonic waves, suspension, etc., by mixing in a prescribed ratio.
對比例Comparative ratio 11
一種液晶組合物,組分及性能參數如表2所示:
表2液晶組合物的組成及性能參數
對比例Comparative ratio 22
一種液晶組合物,組分及性能參數如表3所示:
表3液晶組合物的組成及性能參數
實施例Example 11
一種液晶組合物,組分及性能參數如表4所示:
表4液晶組合物的組成及性能參數
實施例Example 22
一種液晶組合物,組分及性能參數如表5所示:
表5液晶組合物的組成及性能參數
實施例Example 33
一種液晶組合物,組分及性能參數如表6所示:
表6液晶組合物的組成及性能參數
實施例Example 44
一種液晶組合物,組分及性能參數如表7所示:
表7液晶組合物的組成及性能參數
實施例Example 55
一種液晶組合物,組分及性能參數如表8所示:
表8液晶組合物的組成及性能參數
實施例Example 66
一種液晶組合物,組分及性能參數如表9所示:
表9液晶組合物的組成及性能參數
由上表中對比例1-2與實施例1對比可以看出,通過對本發明通式I的化合物的結構優化,並與含有碳碳不飽和鍵的通式II的化合物協同作用,使得包含本發明的液晶組合物在維持基本相當的清亮點、光學各向異性及介電各向異性的前提下,具有更高的垂直於分子軸的介電常數ε⊥ 、更高的垂直介電與介電絕對值的比值ε⊥ /|Δε|及更高的平均彈性常數Kave ,從而使包含該液晶組合物的液晶顯示器件具備更高的穿透率及更高的對比度。From the comparison of Comparative Examples 1-2 and Example 1 in the above table, it can be seen that by optimizing the structure of the compound of the general formula I of the present invention, and synergistically acting with the compound of the general formula II containing a carbon-carbon unsaturated bond, the compound containing this Under the premise of maintaining substantially equivalent clearing point, optical anisotropy and dielectric anisotropy, the liquid crystal composition of the invention has higher dielectric constant ε ⊥ perpendicular to the molecular axis, higher perpendicular dielectric and dielectric constant. The ratio of electric absolute value ε ⊥ /|Δε| and higher average elastic constant Kave , so that the liquid crystal display device comprising the liquid crystal composition has higher transmittance and higher contrast.
由上述實施例1-6可知,本發明的液晶組合物均具有高的清亮點、大的光學各向異性、大的介電各向異性、較高的垂直於分子軸的介電常數ε⊥ 、較高的垂直介電與介電絕對值的比值ε⊥ /|Δε|及較高的平均彈性常數Kave ,包含該些液晶組合物的液晶顯示器件均具備穿透率佳、對比度高的效果。本發明的液晶組合物可滿足液晶顯示器件對功耗低、顯示效果好的要求,在IPS模式、FFS模式及VA模式型液晶顯示器中具有較高的應用價值。It can be seen from the above Examples 1-6 that the liquid crystal compositions of the present invention all have high clearing point, large optical anisotropy, large dielectric anisotropy, and high dielectric constant ε ⊥ perpendicular to the molecular axis , higher ratio of vertical dielectric to absolute value of dielectric ε ⊥ /|Δε| and higher average elastic constant Kave , the liquid crystal display devices containing these liquid crystal compositions have good transmittance and high contrast ratio. Effect. The liquid crystal composition of the invention can meet the requirements of the liquid crystal display device for low power consumption and good display effect, and has high application value in IPS mode, FFS mode and VA mode liquid crystal displays.
申請人聲明,本發明通過上述實施例來說明本發明的一種包含二苯並衍生物的液晶組合物及液晶顯示器件,但本發明並不局限於上述工藝步驟,即不意味著本發明必須依賴上述工藝步驟才能實施。所屬技術領域的技術人員應該明瞭,對本發明的任何改進,對本發明所選用原料的等效替換及輔助成分的添加、具體方式的選擇等,均落在本發明的保護範圍和公開範圍之內。The applicant declares that the present invention illustrates a liquid crystal composition comprising dibenzo derivatives and a liquid crystal display device of the present invention through the above examples, but the present invention is not limited to the above process steps, that is, it does not mean that the present invention must rely on The above process steps can be implemented. Those skilled in the art should understand that any improvement of the present invention, the equivalent replacement of the selected raw materials of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.
以上實施方式只為說明本發明的技術構思及特點,其目的在於讓熟悉此項技術的人瞭解本發明內容並加以實施,並不能以此限制本發明的保護範圍,凡根據本發明精神實質所做的等效變化或修飾,都應涵蓋在本發明的保護範圍內。The above embodiments are only intended to illustrate the technical concept and characteristics of the present invention, and their purpose is to allow those who are familiar with the technology to understand the content of the present invention and implement it, and cannot limit the scope of protection of the present invention. Equivalent changes or modifications made should be covered within the protection scope of the present invention.
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Publication number | Priority date | Publication date | Assignee | Title |
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CN110343531A (en) * | 2018-04-02 | 2019-10-18 | 北京八亿时空液晶科技股份有限公司 | A kind of dibenzothiophenes class can poly- property compound and its application |
TW202003807A (en) * | 2018-05-18 | 2020-01-16 | 大陸商石家莊誠志永華顯示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
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CN110343531A (en) * | 2018-04-02 | 2019-10-18 | 北京八亿时空液晶科技股份有限公司 | A kind of dibenzothiophenes class can poly- property compound and its application |
TW202003807A (en) * | 2018-05-18 | 2020-01-16 | 大陸商石家莊誠志永華顯示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
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